With the advent of Shortcuts on macOS, automation on the Mac has become more accessible than ever. There is no part of our workflows that we can’t automate and thus there is no part of our workflows that we cannot overautomate.

While developing the Podcast Note shortcut that Jason and I collaborated on, I ran into a dilemma. I had just recently adjusted all my Audio Hijack sessions, where I maintain separate instances for most of my regular shows, to save audio files within corresponding subfolders in my Podcasts folder.1 (The impetus was to get those hefty files off my Desktop, which is now synced via iCloud. No need to have several hundred megabytes uploaded to the cloud only to be removed within the hour.)

But that made my Podcast Note shortcut tricky, because it assumes the files it’s looking for will be in a single folder, not strewn through any of several subfolders.

There were a few different ways this could have been solved—I’m sure I could have adjusted the Podcast Note shortcut to search through all the subfolders and find the most recently modified file, for example, but there’s a risk of error, and it feels like at that point I’ve adjusted it to be too specific to my workflow.…